Your Retirement Planning Checklist: 10 Steps to Take Before You Retire

By Clinton Courier | July 3, 2026 |

A good retirement planning checklist turns a vague “someday” into a series of concrete steps you can actually work through. Most people are not unprepared for retirement because they made one big mistake. They are unprepared because the decisions are scattered, easy to postpone, and hard to see all at once.

Putting them in order fixes that. Work through the steps below to understand where you stand, what to prioritize, and where a second opinion is worth the cost.

TL;DR

Estimate the income you will need, add up every source you will draw from, and maximize tax-advantaged savings while you are still working. Then make deliberate decisions about when to claim Social Security, how to cover healthcare, and how to withdraw money tax-efficiently. Revisit the plan yearly, and get professional guidance for the decisions that are hard to reverse.

1. Estimate the Income You Will Actually Need

Start with a target, not a guess. A common planning guideline is that retirees need somewhere between 70 and 80 percent of their pre-retirement income to maintain their lifestyle, though your number depends on your housing, health, and how you want to spend your time.

Map your expected monthly expenses in retirement, separating the essentials from the discretionary. That single exercise tells you whether you are on track or facing a gap, which is the most useful thing any retirement planning checklist can do early.

2. Add Up Every Income Source

List everything you will draw from: Social Security, any pensions, retirement accounts, taxable savings, and income from work or rentals. Seeing them together shows how much has to come from your own savings versus guaranteed sources.

The Social Security Administration lets you create a free account at SSA.gov to see your estimated benefit based on your actual earnings record. Check it early, because that figure is often the anchor the rest of your plan is built around.

3. Maximize Tax-Advantaged Savings Now

The years right before retirement are your last and best chance to add to tax-advantaged accounts. Contribute as much as you reasonably can to a 401(k) or IRA, and take advantage of catch-up contributions if you are 50 or older.

The IRS adjusts contribution limits most years, so confirm the current figures rather than relying on last year’s numbers. Even a few additional years of maxing out these accounts can meaningfully change the income your savings produce later.

4. Get Your Social Security Timing Right

When you claim matters as much as how much you have saved. You can start benefits as early as 62, but claiming before your full retirement age permanently reduces your monthly check, while waiting until 70 increases it.

There is no universally right answer, since the best choice depends on your health, your other income, and whether a spouse is involved. This is one of the highest-stakes, hardest-to-reverse decisions on the list, which is why it deserves real analysis rather than a rule of thumb.

5. Plan for Healthcare and Long-Term Care

Healthcare is the expense most people underestimate. Medicare eligibility begins at 65, so if you retire earlier you need a plan to bridge the gap, and even with Medicare you will face premiums, copays, and costs it does not cover.

Review your options early through the official Medicare.gov resources, and think honestly about long-term care. The cost of extended care is one of the largest risks to an otherwise solid plan, and it is far easier to address before you need it.

6. Build a Tax-Smart Withdrawal Strategy

How you withdraw money affects how long it lasts. The order in which you tap taxable, tax-deferred, and tax-free accounts changes your lifetime tax bill, sometimes significantly.

Required minimum distributions eventually force withdrawals from certain accounts, which can push you into a higher bracket if you have not planned ahead. Coordinating withdrawals, Social Security timing, and tax brackets is where thoughtful planning pays for itself.

7. Turn the Checklist Into a Plan

A checklist tells you what to consider. A plan tells you what to do, in what order, for your specific numbers. This is the step where many people benefit from an outside perspective, especially for the decisions that cannot be undone.

A fee-only fiduciary practice like Even Path focuses on exactly these transitions, helping people pressure-test their assumptions before they commit. If you want a structured second opinion, professional retirement guidance can be the difference between hoping you are ready and knowing it.

Retirement Planning Checklist at a Glance

Keep this short version where you can revisit it each year:

Set an income target: Roughly 70 to 80 percent of pre-retirement income, adjusted for your life.
Inventory your income sources: Social Security, pensions, savings, and other income.
Max out tax-advantaged accounts: Including catch-up contributions after 50.
Decide on Social Security timing: Weigh claiming early against waiting.
Build a healthcare plan: Bridge any gap before 65 and budget for long-term care.
Plan tax-smart withdrawals: Mind the order of accounts and required distributions.
Review annually: Adjust as your life and the rules change.

Final Word

Retirement planning rarely fails because of one dramatic error. It succeeds when ordinary decisions get made on purpose instead of by default. Work through this retirement planning checklist one step at a time, revisit it each year, and bring in help for the choices that are expensive to get wrong. Do that, and retirement stops being a source of background worry and starts looking like something you have genuinely prepared for.